The summer between my seventh and eighth grade of school, my parents took a two-week vacation to Europe. Though I thought I was old enough to take care of myself, my parents felt there should be someone to look after me and the house while they were away.
My parents hired Kate, the 19-year-old daughter of one of our neighbors. Kate, who wanted to earn some money before going off to her sophomore year of college, was happy to take the job.
I occasionally saw Kate around the neighborhood but being seven years younger than her, didn't know her very well. Kate had dark brown hair, was 5'8', which was taller than me at the time, and had a lean body from playing sports in school.
The first few days of Kate's stay were uneventful. She pretty much left me alone to do whatever I wanted. Towards the end of the first week, however, I got the idea of looking through Kate's stuff while she was out running an errand. I made my way up to the guest bedroom where Kate was staying. There I found a large duffel bag full of Kate's clothes and more importantly, her panties, a nice mix of briefs and thongs.
I had started masturbating on an almost daily basis a few years before and quickly found myself becoming aroused. I smelt the crotch but being clean, the panties had little odour. Fully aroused, I pulled down my shorts, wrapped the panties around my cock and slowly moved my hand up and down. It wasn't long before I felt the inevitable rush of an orgasm come over me. I pulled the panties away just in time before I pumped a load onto my hand and the floor. I quickly cleaned up and placed the panties back in the bag where I found them.
A couple of days later, when Kate was out again, I snuck up to her room and found a small laundry bag where Kate kept her dirty clothes. This time I found her dirty panties. The pair I picked were dark blue with light blue polka dots. They even had the faint smell of Kate on them. I quickly undressed and wrapped the panties around my cock. I slowly moved them up and down, enjoying how the silky fabric felt, thinking about how Kate would look in them. As I became more aroused, I picked up my pace, moving my hand quickly up and down the length of my cock. Knowing that her panties were destined for the laundry, I held them firmly around my cock and let myself explode into the folds of the soft fabric. It was incredible. When I was finished, I cleaned up and buried the panties in the middle of the bag.
This was so great. If only I could catch Kate coming out of the shower or spy on her changing in her room. I loved my new found masturbatory technique and as the week went on I looked for every opportunity to make my way up to Kate's room.
The only catch was that she was always home, when I was home. I was getting hornier and hornier thinking about Kate and her panties. Two days before my parents came home, I found my opportunity.
I was watching TV when Kate came downstairs in a swimsuit and said that she was going to sunbathe in the backyard. I could hardly take my eyes off her as she walked out of the back door. Once she was outside I ran upstairs to the window to spy on her from above. Just my luck, a tree blocked most of her body and I could only see her legs.
On to Plan B. I would run into her bedroom and toss off a quick one with a pair of her panties before she came back inside. I knew I would hear if she came back inside but didn't know how much time I would have to get myself back together so I left my clothes on and just pulled down my shorts. This time, I grabbed a pink thong out of Kate's laundry bag and quickly went to work. I decided I liked the dirty underwear more because I could cum in them.
Knowing I might only have a few minutes, I moved my hand furiously up and down my cock. Only a minute or two passed and I was nearing orgasm. That's when I heard something. Oh shit, she's downstairs I thought to myself. Have to move fast. Kate's panties in one hand, hard-on waving in the air. I reached down to pull up my shorts. That's when Kate appeared in the doorway.
Not expecting to see me, Kate was startled. Her surprise quickly turned to anger though when she saw me with my pants down and her panties in my hand. My face flushed crimson. 'I'm sorry. I'm so sorry, it won't happen again,' I said pulling my shorts back up. My cock quickly deflated. 'You're damn right it won't happen again,' she shot back, 'That is so gross. I can't believe you were jacking off with my underwear you little pervert.' 'I'm sorry. Please don't tell anyone,' I asked. 'Of course I'm going to tell someone,' she said. 'Your parents are going to kill you when they find out. I'm going to go and e-mail them right now and tell them what a little freak their son is.'
'No, please don't tell them. Please don't tell them' I pleaded. 'Why shouldn't I? You've probably been jacking off with my underwear for the past two weeks.' With that she grabbed her laundry basket and dumped her clothes out onto the bed. She separated out her panties and quickly found the blue polka dot pair I had shot my load into a couple of days before. 'You little shit,' she said looking at the cum-encrusted panties. 'You are so dead.'
She then sat down on her bed and her eyes burned into me. She didn't say anything, she just stared at me as the gears of her mind turned.
The silence was killing me. 'Please don't tell my parents,' I pleaded again. She just stared. Finally she said, 'Fine, I won't tell your parents.' 'Thank you, thank you so much,' I said. 'This will never happen again.' I then started to back out of the room.
'Where do you think you're going?' she said. 'You're not going anywhere.' 'Huh? Oh, I'm sorry,' I repeated. 'No you don't get it,' she said. 'I may not tell your parents but you still have to pay for what you did. Get over here.' Confused, I walked over to the side of the bed where she was sitting. 'Drop your shorts and get over my lap,' she said.
'What?' I said. Then it hit me. 'You're nuts. You can't do that. You can't spank me. I'll tell my parents.' 'Fine, go ahead,' she replied, 'And, I'll tell them just what you've been up to with my underwear and I have the proof,' she said holding up the soiled panties. 'But I, uh...' 'No buts about it, except your butt! Now drop and get over my knee!' I ran all the options through my mind and not seeing any way out of this, I lowered my shorts and went to get over her lap.
'Those too,' she said pointing at my briefs. 'And your shirt.' My face turned even redder than it already was, if that was possible. Other than my mother, no other woman had seen me nude before. I slowly stripped and at last stood in front of her with my hands covering my crotch. 'Now, let's see what we have here,' she began. 'Move your hands.' 'But I...' 'You have absolutely no say in this and unless you want me to tell your parents, you will do exactly what I tell you to do. Now, as I was saying, let's see what we have here.' She gestured for me to move my hands, which I reluctantly did.
'Kind of small but I suppose you're still young.' she said. 'But not so young that you shouldn't know better than to do what you did. Get over my lap.' This was all so new to me. My parents didn't even spank me when I was younger. I slowly lowered myself onto her bare lap, my soft cock resting against the tops of her legs. 'Don't you know how wrong it is to go through other people's things?' she went on as she grasped me and put her left hand on my back. 'It doesn't matter. For jacking-off with my underwear I'm going to spank your little white ass until it's bright red.'
The first spank came as a shock. It was quickly followed by more. I soon felt a warmth and then a stinging sensation spread across my butt as she spanked me. 'Doesn't feel good does it?' she said. Not letting me answer, 'Do you jack off in your mother's underwear too?' No!' I wailed. 'I doubt that.' she said.
SMACK SMACK SMACK SMACK
'Are you going to do it again?' 'No.' 'I thought you said you don't jack off in your mother's underwear?'
'No, I meant...' Not letting me answer again, 'How many times did you jack off with my underwear?' 'Just twice,' I said. 'Liar!'
SMACK SMACK SMACK SMACK.
As Kate began to spank harder, she repositioned her legs so that she could have better leverage while hitting my ass. Between my squirming and her legs moving apart, my cock slipped between her thighs. 'Now tell me, how many times did you jack off with my underwear?' she asked again. 'Three times,' I said, hoping she would stop.
SMACK SMACK SMACK SMACK
'That's better. Are you going to lie to me again?' 'No,' I barely managed to say. 'I can't hear you.' 'No,' I said louder. 'Damn right you won't lie to me again.'
SMACK SMACK SMACK SMACK
As if I wasn't embarrassed enough with my now red ass pointing up in the air at Kate's face, the friction caused by Kate's thighs against my cock was arousing me again. I don't know if she felt it our not but my cock grew harder and harder as she spanked me. 'I bet you jack off that little cock of yours every day, don't you?' I hesitated. 'Don't you?' she said louder. 'Yes,' I answered. 'I thought so. Now don't make me keep repeating myself.'
SMACK SMACK SMACK SMACK
With her free hand, Kate grabbed the blue panties off the bed and shoved them up to my nose. 'Did you smell my pretty panties,' she said. 'Yes,' I replied. 'Then you're going to like this you little pervert,' She pushed them against my lips and stuffed them in my mouth 'There,' she went on, 'taste good?' as she continued the hard spanking. The spanking was almost unbearable now but I could barely contain myself. I had been so close to coming before she caught me in the act and now having my cock rub between her thighs, I was going crazy. She spanked me a few more times and then stopped. She gently rubbed my sore butt for a moment. 'I don't enjoy this and I'm sure you don't enjoy this but you can't do what you did. Do you understand? 'Yes,' I mumbled with the panties still in my mouth, 'I'm going to give you 10 more just so that you realize how bad you were. I want you to count them.'
SMACK 'One' Smack 'Two' SMACK 'Three' And on she went. It was on number seven that my balls tightened and I exploded my load onto her thighs and the bed, the panties in my mouth stifling my gasp. It was the most amazing orgasm I'd ever had. I felt weak and nearly went limp on Kate's lap.
Feeling my pulsating cock and the wetness on her lap, Kate pushed me off her lap and onto the floor. 'You brat!' she screamed. 'Get me something to clean this off with.' I ran to the bathroom and grabbed towels for both of us. We cleaned ourselves off, while she cursed at me for coming on her. It was when I went to get dressed that I realized she wasn't through with me.
'What do you think you're doing,' she barked. 'Get your ass over in that corner. Face the wall.' Kate made me face the wall for an hour while she watched TV before letting me get dressed.
I have no idea what Kate is doing today but I often think back on that extremely embarrassing but sexually amazing moment in my life.